Staircase Ventures — Investment Thesis & Preferences

01Investment Thesis

Lead pre-seed and seed rounds in Canadian B2B software and AI-enabled vertical workflow companies with an initial product in market, early product-market-fit signals, and ambition to scale across North America or globally.

Exclusion Criteria

No explicit exclusions found. Public materials imply weaker fit for later-stage companies, companies outside Canada, non-software businesses, companies without an initial product or early customer evidence, and founders seeking only passive capital.

02Investment Team

JB

Janet Bannister

Founder and Managing Partner

AT

Andrew Tiffin

Operating Partner

JR

Jy Rivera

Executive Assistant

MW

Mike Wessinger

Advisor

CM

Craig Miller

Advisor

AK

Ahmed Khaishgi

Advisor

KH

Kristen Hamilton

Advisor

AP

Angelo Papatheodorou

Advisor

MV

Manoj Verma

Advisor

MS

Mike Shaver

Advisor

DB

David Belbeck

Advisor

03F4 Research Brief

Staircase Ventures Research

Investment Thesis

Staircase Ventures is a Toronto-based early-stage venture firm founded and led by Janet Bannister. The firm positions itself around founder development as much as capital: it leads pre-seed and seed rounds in Canadian technology companies and pairs investment with a structured Founder Growth Platform, shared carry for portfolio founders, board-level involvement, and access to experienced advisors who have built large technology companies. Its homepage states that Staircase leads seed-stage rounds in Canada's highest-potential technology companies and has unusual dedication to accelerating founder development and performance. The investment focus section says the firm primarily invests in B2B software companies that use technology to deliver radically improved efficiency or effectiveness for customers.

The portfolio shows a clear preference for Canadian B2B software and AI-enabled vertical workflow businesses. Examples include Mave for residential real-estate agents, MedEssist for retail pharmacy clinics, DBGorilla for database administration, Ultimarii for regulatory and legal approvals on infrastructure projects, Una for financial planning, Sibli for investment research, Rhenti for residential rental leasing, Fillip for fleet payments, Galatea for waste logistics, Tengiva for textile commerce, and Biossil for applied AI drug discovery. The public materials repeatedly frame AI as a way to make specialized workflows faster, more accurate, and more efficient, but the firm is not a general AI-only fund; it appears most interested when AI or software is attached to a concrete vertical workflow and a large customer pain.

Stage Focus

Staircase focuses on pre-seed and seed. The homepage says the firm leads pre-seed and seed rounds, looks for companies with an initial product in market, and wants early signs of product-market fit. The Fund II launch post said Staircase had invested in 12 portfolio companies over its first three years and planned to continue the same concentrated strategy. BetaKit's Fund II coverage reported that Fund I included nine seed investments and three pre-seed investments. That makes Staircase a strong fit for Canadian founders who have built an early product and can show customer evidence, and a weaker fit for later-stage companies, pure services businesses, or teams still at the idea-only stage.

Check Size

The firm's current homepage says Staircase leads pre-seed and seed rounds with cheque sizes between $1 million and $2 million. BetaKit's March 2026 coverage of Fund II reported that Staircase planned to write $1 million to $2.5 million initial cheques and reserve 40% for follow-on financing. For matching purposes, the best current range is $1 million to $2.5 million, with the narrower public homepage band anchoring the core initial check.

Lead Tendency

Staircase is strongly lead-oriented. The homepage says it leads pre-seed and seed rounds, and individual investment announcements use the same language: Staircase led or is leading Mave, MedEssist, DBGorilla, Ultimarii, Una, Fillip, Biossil, Rhenti, and Sibli. Its philosophy page says Janet Bannister takes a seat on every company board and works actively with founders and teams to set the business on a path for long-term growth. Founders should expect Staircase to be a hands-on lead investor rather than a passive syndicate participant.

Recent Activity

Staircase is actively deploying from Fund II. On November 17, 2025, it announced an initial $32 million close for Staircase Ventures Fund II. On January 4, 2026, it announced Andrew Tiffin had joined as Operating Partner after Shopify, Uber Eats, Clutch, and RenoRun operating roles. On January 13, 2026, Staircase announced it led MedEssist's most recent funding, and on January 20, 2026, it announced it was leading Mave's seed-stage round. On March 9, 2026, the firm announced it had closed a $50 million Fund II that exceeded its $40 million target and brought in new LPs including BDC, University of Alberta, and InBC.

Portfolio Highlights

The official portfolio page lists Banting AI, Biossil, DBGorilla, Eventric, Fillip, Galatea, Mave, MedEssist, Rhenti, Sibli, Tengiva, Ultimarii, and Una. The strongest portfolio pattern is B2B software for operationally complex markets: health care and life sciences, real estate and property operations, developer and data infrastructure, financial planning and investment research, fleet payments, waste logistics, textiles, and event operations. Several portfolio companies have AI as the core product or an important feature set, but Staircase's investment rationale usually ties AI to workflow automation, customer ROI, operational efficiency, and founder-market fit.

Team

Janet Bannister is Founder and Managing Partner. Her Staircase profile says she previously served as Managing Partner at Real Ventures, founded Kijiji.ca, worked at eBay in Silicon Valley, and has more than a decade of early-stage technology investing experience in Canada. Andrew Tiffin is Operating Partner; Staircase's January 2026 announcement says he joined after Shopify, where he was Chief of Staff to the CRO and led Merchant Services Product Operations, and that he supports portfolio companies on finance, organizational design, go-to-market systems, pricing, growth strategy, tooling, sales compensation, and AI ROI. Jy Rivera is Executive Assistant. The advisor group includes operators from PointClickCare, Shopify, SquareTrade, Koru, TabaPay, Fastly, and other scaled technology companies.

Decision Process

Public sources do not disclose a fixed investment committee process or decision timeline. The firm appears Janet-led, with Andrew Tiffin and the advisor network supporting diligence, founder development, and portfolio operations. Decision criteria are more visible than mechanics: product in market, early product-market-fit signs, a large market, a technology or AI wedge that improves efficiency, deep customer understanding, speed of execution, founder grit, growth mindset, strong leadership, and the ability to attract strong talent. Because no public source states a timeline, that field is intentionally omitted.

Founder Preferences

Staircase prefers Canadian founders building ambitious B2B technology companies and willing to work closely with a high-touch lead investor. Its investment posts repeatedly praise founders for industry experience, operating discipline, customer empathy, complementary founding teams, grit, hustle, and growth mindset. The five-pillar support platform and carry-sharing model suggest a strong preference for founders who value coaching, peer learning, advisor access, health and wellness support, family support, and a close founder community.

Geographic Focus

The primary geography is Canada. The homepage says Staircase invests in Canadian-based companies, most of which target North American or global markets. Portfolio companies are concentrated across Canadian ecosystems including Toronto, Calgary, and Montreal, while many sell into broader North American or global enterprise markets.

Sources

Homepage and investment focus: https://staircaseventures.com/
Portfolio: https://staircaseventures.com/portfolio-companies/
Team: https://staircaseventures.com/our-team/
Philosophy: https://staircaseventures.com/our-philosophy/
Janet Bannister profile: https://staircaseventures.com/team/rachel-m-12/
Andrew Tiffin profile: https://staircaseventures.com/team/andrewtiffin/
Fund II close: https://staircaseventures.com/staircase-ventures-closes-50-million-fund-ii/
Fund II launch: https://staircaseventures.com/staircase-ventures-launches-fund-ii/
Mave investment: https://staircaseventures.com/staircase-ventures-announces-investment-in-mave/
MedEssist investment: https://staircaseventures.com/staircase-ventures-announces-investment-in-medessist/
DBGorilla investment: https://staircaseventures.com/staircase-ventures-announces-investment-in-dbgorilla/
Ultimarii investment: https://staircaseventures.com/staircase-ventures-announces-investment-in-ultimarii/
Una financing coverage: https://staircaseventures.com/press/una-software-secures-new-seed-funding-as-startup-adds-ai-into-its-financial-planning-platform/
Sibli financing coverage: https://staircaseventures.com/press/staircase-ventures-bets-on-sibli-as-vc-firm-reveals-first-four-investments/
BetaKit Fund II coverage: https://betakit.com/janet-bannisters-staircase-ventures-closes-50-million-second-fund/